Jesse Draper has heard it all: “nepo baby,” “charity fund,” “too niche”—and she turned every jab into fuel. After getting laughed out of rooms while raising her first fund, Jesse built Halogen Ventures into one of the earliest venture capital funds explicitly focused on backing female founders, now with 85+ portfolio companies and multiple unicorns.
In this episode, Jesse breaks down how she actually evaluates startups when they’re early (and sometimes barely making their first dollar), the metrics she thinks founders overhype, and the green flags that make her lean in, like radical transparency and founders who are obsessed enough to “check QuickBooks” mid-question. She also tells the wild story of why she’ll never invest off Zoom again, how social media has changed consumer investing, and what the DEI rollback is starting to look like inside venture.
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Here’s what Sammi covers with Jesse
00:00 Jesse Draper’s Social Currency
00:50 Meet Jesse Draper
03:00 The Reality of Being Fourth Generation VC
06:13 The Valley Girl Show and the Elon Musk Interview
16:36 From Entertainment to Entrepreneurship
18:25 Getting Laughed Out of Pitches and Championing Female Founders
25:36 Crazy Pitch Stories
27:25 The Wild Con Artist Story
30:29 Never Invest Based on Zoom Meetings
34:03 The Viral “Investing In Women Is Not a F*cking Charity” Essay
37:16 Data That Investing in Women Works
38:09 What Founders Should Know About Conversations with VCs
41:43 Red Flags and Green Flags
46:44 How Social Media Has Changed VCs
53:00 Future of Equity in VC
59:12 Investing in Alabama
01:07:56 Social Currency Corner
01:09:57 How to Show Social Currency Some Love
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